


Project Sassy

by jadekirk



Series: The James Tales: Life and Times of a Chef [6]
Category: Supernatural
Genre: Crack, M/M, Matchmaking, Multi, Other
Language: English
Status: In-Progress
Published: 2011-11-02
Updated: 2011-11-11
Packaged: 2017-10-25 15:19:00
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 2
Words: 3,797
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/271785
Author URL: https://archiveofourown.org/users/jadekirk/pseuds/jadekirk
Summary: <blockquote class="userstuff">
              <p>A crazy matchmaking plot spells chaos for Sam and Castiel when James and Dean try to get them together.</p>
            </blockquote>





	1. Making Plans

**Author's Note:**

> My first time writing the Sam/Castiel pairing. Hope it's okay. One of these days I will write the fic in which James joins the team. AU from 'Swan Song' so Sam came back in one piece and a certain character wasn't killed off.

  
**Sam**   


"James, I need to talk to you," Sam said, making James look up from where he was lying on the bed, reading a book, which was titled 'The Cat Who Lived High' in surprise.

Sometimes it was easy to forget that James had joined their ragtag bunch of misfits only two years ago as he seemed to slot into place pretty well. James was a tall, deceptively slim looking, red haired man, standing about the same height as Dean, with warm brown eyes. Sure, the red head was snarky and grumpy in the morning before coffee, but he also was laid back and easy going and nothing seemed to shock him. James had told them that he was originally from Scotland but he now lived in Cardiff and he worked as a chef for one of the military bases there. "It definitely isn't boring," he had commented afterwards.

James put the book to one side and looked up expectantly at Sam. "Well, first things first, sit down" he ordered in his deep Scottish accent, as he swung his legs around so he was in a sitting position. "You're giving me a crick in the neck."

Sam flushed and sat down on the bed opposite the red head. "Sorry."

"So what can I do you for?" James asked. He noticed Sam was looking down at his hands. "All right, spill. What's bothering you? You wanted to talk to me and now I'm all ears. So what is it?"

"IthinkImighthavefeelingsforCas," Sam mumbled without looking up from his hands.

James rolled his eyes. "What was that?" he asked, not sure if he had heard right. "Again, and this time with actual spaces between the words."

"I think I might have feelings for Cas," Sam admitted, not seeing the triumphant grin that had crossed James' face at his admission.

James schooled his face into an intrigued expression when Sam looked up. Inside he was doing the mental macarena as he had been waiting for this moment. He had noticed the sexual tension between Sam and Castiel and he and Dean had been waiting for at least one of them to admit it. "I see," he said. "And how long has this been going on?"

"I don't even know if he likes me. I mean, he talks to Dean more than me and he likes you."

"Of course he likes you," James commented. "I mean, he could smite me if I looked at him wrongly. Not the kinda bloke you want to get on the wrong side of. You're still here, aren't you?"

"That was blunt."

"Say it as I see it. And you didn't answer my question. How long?"

"That's why you and Dean are perfect for each other... A while."

James raised an eyebrow. "Are you now pairing Dean and myself off? Who are we talking about here again?"

Sam flushed, but looked up at James. "He's definitely your type. Can't leave you and Dean feeling left out."

James shrugged. "You know what I always say, sharing is caring."

"I swear you were a Roman Emperor in a previous life. I can just see you in a toga and orgies everywhere."

James chose to not answer Sam's comment. "Sam, we're speaking about you and Cas. So what do you want me to do about it?"

"How to get him to notice me."

"I swear he's noticed you. Alaska ringing any bells?"

"That was different. It was a survival thing."

James fought the urge to facepalm and settled for a mental one instead. "Have you tried talking to him?"

"I can't. I- I just sound so... stupid."

"Sam, look at me," James said, moving to sit next to Sam. "You aren't stupid. All you need to do is talk to him. It's easy."

"Easy for you to say. You have the looks and that sexy accent and you have people falling at your feet."

"It's not easy being me." James sighed. "Anyway, back to you and Cas. Just say to him, preferably when Dean and myself aren't there, 'Hey, I got a thing, you're maybe feeling a thing, and there could be a thing'. Although, maybe not in those exact words."

Sam frowned as he recognised where James had gotten the quote from. "Thank you, Buffy. Do you think it'll work?"

"Buffy's hot. I'm sure it will."

"You think everyone's hot."

"Why limit myself?" James sighed again. "Look, I'm ninety nine percent sure that all the poor angel is waiting for is for you to make the first move. So do so."

"Are you this bossy back in Cardiff?"

"Yes. If I'm wrong about it, we could both get zapped by Cas."

 

 **  
Castiel   
**

 

"Dean, I must speak with you," Castiel announced as soon as he had appeared in front of Dean, making him jump and choke on his drink.

"Damn it, Cas! Don't do that!" Dean said, once he got his heart beat back to normal and the coughing had subsided. "So what's up?"

"I wish to know how to proceed in courting your brother."

"Sam?"

"Yes."

"And you want to do the horizontal tango with Sam?"

"I don't understand..."

"Have sex with him."

"Yes. So will you help?"

"You want me to set you up with my brother?!"

"Please."

Dean had to pause at that. Castiel almost never said 'please' and for him to do so must mean he's serious. "Fine." He secretly wondered when he had become his angel and brother's relationship advisor and decided to blame James for it since he was the one who had first noticed it and had decided to drag Dean into his little matchmaking scheme.

 ****Flashback****

 _"Dean," James said once Castiel and Sam had left the room to get coffees, "why aren't Sam and Cas shagging already?"_

 _"Dude, what?" Dean asked, looking confused, whether it was because of the British slang that the tall red head had used or whether he was wondering why James had suddenly decided to pair off his brother and friend, James wasn't sure. "Shagging?"_

 _James rolled his eyes. "Do I have to get out the British slang dictionary again? You already found out what it meant."_

 _"Yeah, but then you wandered out from the bathroom wearing that very small towel and I got distracted."_

 _James flicked Dean's ear, eliciting a yelp of surprise from him. "Dean, focus!"_

 _"Why are you even interested?" Dean questioned, holding his ear and scowling at James._

 _"Because the UST is driving me insane. Well, insaner than usual."_

 _"How can it be UST if it's been resolved?"_

 _"Alaska doesn't count," James stated, flushing slightly. "Besides 'needs to be re-resolved unresolved sexual tension' makes for a bit of a mouthful or for one of a hell of a acronym."_

 _"You'd know all about mouthfuls wouldn't you, James?"_

 _"Bite me."_

 _"You'd enjoy it."_

 _James shrugged, not bothering to confirm or deny that claim. "Anyway, back to Sam and Cas, their not so secret longing for each other is just... distracting. We need to get them together."_

 _"I thought you had a thing for Cas," Dean pointed out._

 _"I do, and Sam and you too... But I know how to share," James said with a wink._

 _"You're very kinky."_

 _"You only just realised that? I'm very flexible."_

 _"I noticed. So how would we do this matchmaking thing?"_

 _James flopped down on one of the beds, propped himself up on his elbows and looked at Dean. "Well, we have to get them in the position of admitting their feelings. And, no, I'm not getting Cas to beam us to Alaska and then injuring the poor bloke so he can't beam back until he's at least snogged Sam. It's too cold for one."_

 _"Snog?"_

 _"Kiss," James explained with a roll of his eyes._

 _"I think you like to use the Brit slang deliberately just to confuse us," Dean accused, pointing at James. "You're from Scotland. You should be used to the cold."_

 _"I haven't lived in Scotland for years. Stop changing the subject. Or I'll get Gabriel to help me."_

 _"No! He'll do something with a pair of handcuffs and chocolate body paint. Remember what happened on your last birthday?"_

 _"The pony was your idea. The strippers were Gabe's."_

 _"What about the tentacles?"_

 _"I'm beginning to think you have a hard on for the tentacles. Quit trying to distract me."_

 _"You really are bitchy if you don't get enough coffee, aren't you?"_

 _"I'm only bitchy if a certain person, who is right in front of me, keeps giving me holy water wakeup calls."_

 _"You get loud and pornographic. I have to wake you before our neighbors get the wrong idea. We aren't in Alaska anymore."_

 _"Do not. I'm sharing with you tonight. At least then I can push you onto the wet patch."_

 _"You can try."_

 _James gave him a look. "Are you going to help me or not?"_

 _"What's in it for me?"_

 _James shot Dean a long look. "I'll take you to a strip club," he promised. "I'll even buy the drinks."_

 _"Okay. You going to dance again?"_

 _"Why?"_

 _"You're good at it. Get lots of tips. What do they teach you over there?"_

 _"In Cardiff?"_

 _"Yeah."_

 _"Lots of things," James answered with a smirk._

 _"That what they teach you in chef school?"_

 _"Nah, that came later."_

 _"I bet. Why did you snicker when Sam told you he was going to be Agent Tyler when we did that case with the mermaid?" Dean asked, changing the subject again. "And then ask if he got hit by a car and sent back to nineteen seventy three?"_

 _"It's a Brit thing," James answered mysteriously. "I hear the Internet has the answers to almost everything." He frowned. "Is that why you only get two beds in the rooms that we stay in? Are you hoping for a little pairing up of your own?" he asked with a mischievous quirk of his eyebrow._

 _"Don't even go there," Dean warned. "So where do we begin?"_

 _"Step one in Project Sassy..."_

 _"Sassy?"_

 _"It's the codename for getting Sam and Cas together."_

 _"Right."_

 _"As I was saying, step one is getting them to admit it."_

 _"And how are we going to do that?"_

 _"Leave it to me."_

 

 ****End Flashback****

Damn James for putting the idea in his head and now, Dean couldn't stop noticing the shy glances between Sam and Castiel when they thought the other man wasn't looking at them. He looked at the angel beside him and sighed. "Sure, I'll help you."

Castiel nodded. "I think we should get back. Sam and James are probably wondering where we are."

Dean sighed. "Fine. Beam me away, Cas."

Both men arrived in the motel room just as James was saying, "... get zapped by Cas."

"Oh, you're back," Sam said with a grin.

"Who would get zapped by Cas?" Dean asked, looking between the two men. He almost missed the grin sent his way by James. 'That can't be good... Can it?'

"Daleks," James answered at the same time Sam said, "Clowns."

Castiel tilted his head and gave James a look. "I see."

James quirked a challenging eyebrow at Castiel in reply and mentally recited Nine Inch Nails lyrics in his mind until the angel turned away, his cheeks slightly flushed.

"Your taste in music is... intriguing," Castiel said finally.

"That'll teach you to try and read my mind," James growled. Mind reading was a sensitive subject with the red head and he'd refuse to say why exactly. Dean, Sam and Castiel didn't push it as they had their own wounds to lick. He suddenly switched subjects. "Sam was talking about having a toga party," he blurted.

"That's not what I said!" Sam spluttered, blushing slightly.

"Well, you said a lot of things but I got the gist of you wanting a toga party," James stated, secretly enjoying Sam's embarrassment. "There also was something about orgies in there as well."

"Sammy?!" Dean said finally. He wondered what the red head and Sam had been talking about.

"I compared James to a Roman emperor," Sam explained.

"You know that explains a lot..," Dean said thoughtfully as he sat down next to James. "I like the way he thinks."

"Sam or James?" Castiel questioned.

"Maybe we could have a orgy of our own," Dean continued.

"Four people does not an orgy make," James said, sounding too sure of himself.

"Speaking from experience, Yoda?"

James shoved Dean. "I'm not small, green and wrinkly. Wouldn't you like to know?"

"Yeah. Something else you learned in chef school?"

"Why is it every time I do something, you always ask if I learnt it in chef school?" James asked. "I mean, it's almost like you think I don't have a life otherwise."

"I need a drink.... or twelve."

"You and me both," James commented. "Cas and I will get the booze. And some Jaffa Cakes." James gave Castiel a look that promised that the angel would get interrogated once they were out of earshot of Sam and Dean.

Dean knew that look and decided to do a bit of grilling of his own towards Sam. "Fine, whatever. Hurry back."

"Come on, Cas. Those Jaffa Cakes are calling me."

TBC


	2. Jaffa Cakes and Alcohol

**Sam**

 

As soon as James and Castiel had vanished to wherever they went to get the aforementioned Jaffa Cakes and alcohol, Dean metaphorically pounced on Sam like a lion onto a wildebeest. "So, anything we need to know?"

"Like what?" Sam asked, trying and failing for casual as he wasn't sure what his brother knew.

"Oh you know. Anything at all?"

Sam shook his head. "No," he lied as he was unsure on how Dean would react to Sam's feelings for Castiel.

Dean fixed him with a look that seemed to say that he could look right through his brother and wasn't falling for his lies. "You sure about that?"

"Yeah. Why?"

"The last time you kept secrets from me..."

"Dean, don't." Sam took a deep breath, unsure at what he was going to say next. "I think I have feelings for Cas." Okay, that wasn't what he wanted to say.

"Oh, is that all?" Dean asked, surprising Sam. "Yeah, I knew. James did too."

"He did?" Sam asked. _And he let me tell him that I had feelings and didn't let on that he already knew?_ "Are you okay with that?"

"I need a lot of alcohol before I even answer that, Sammy. But if you hurt him, I will hurt you."

"Is this some twisted version of the protective big brother thing?"

"Does Cas know that you have feelings?" Dean asked, avoiding the question.

"No."

"Tell him."

"I can't."

"Why the Hell not?"

"Because I... I just can't."

Dean sighed and scrubbed at his face, looking like he was about to smack Sam for his reluctance to tell Castiel how he feels.

"Besides, I'm not sure if he likes me in that way."

"Trust me. He does."

"How do you know?"

Dean didn't answer. "Just tell him."

"I didn't expect to see you on board the 'my brother has feelings for a male angel, let's get them together' train."

"Maybe I'm getting mellow in my old age."

Sam snorted. "If you're old, what does that make James then?"

"A very old man. Can't believe he's over fifty years old. He only looks in his thirties."

"He looks good for his age."

"Stop changing the subject, Sam."

"You sound like him."

"Guess he's rubbed off on me then."

"He's definitely rubbed off on Cas. Green body paint springs to mind."

"Sam!"

"Well, who else would rub it over him?"

"Aren't you jealous?"

"Of James? No. It's his way. Besides, James would be willing to share."

"True. He has a twin brother."

"So does Jimmy."

"I know. You looked like you were about to wet yourself in excitement when Cas said that."

"Shut up."

"Make me." Dean was quiet for a moment. "So, when's the wedding?"

Sam gave Dean one of his patented bitchface looks. "Dean..."

"Don't bitchface at me. You have to tell him."

"No, I don't."

"You do because he needs to know. How long?"

"How long, what?"

"How long have you had these feelings?" Dean questioned. "Before or after Alaska?"

Sam didn't answer his brother. He just hoped that James and Castiel would return shortly so Dean wouldn't ask him any more questions.

 

A rush of wind indicated that James and Castiel, laden down with shopping bags, some bearing the unfamiliar name of Tesco on them, had arrived back in the room. Sam noticed that James' shirt was ripped and bloodstained and Castiel's coat was sooty. "What the hell happened to you two?"

"Demons," James answered, placing the bags on the floor. "We got the booze though. Cas was awesome. He zapped most of the demons like he was nuking a pizza."

"While you stood back and sang '99 Problems'. It was only when they trapped me in the ring of holy fire you stepped in."

"Thought you could use a bit of background music," James commented with a wave of his hand as he inspected the damage to his shirt. "I liked this shirt. I'm not injured!" he added as Sam moved over to see if he was hurt. "You were on a roll, Cas. Didn't want to get in your way. You're way too awesome for me. Had to go to England for the Jaffa Cakes. Cas just lands us in the middle of the cat food aisle, scaring the crap out of the lad just about to turn into it."

"I believe his name was James also," Castiel added. "And he appeared to be in his early thirties."

"It was and he's still younger than I am," James confirmed in a voice that suggested he knew exactly who this other person was but wasn't going to say. "Don't say it," he added to Castiel, pointing a finger at the angel for emphasis. "I get enough of that from Jack." He crouched down and rummaged around in the Tesco bags. "I got you some pies, Dean," he said, pulling out a box labelled 'Mr Kipling Bramley Apple Pies' and handing it to Dean. "All the way from the UK."

"Thanks Dude!"

"You look like you brought enough drink to sink the Titanic," Sam commented, automatically ducking when James threw a packet of sweets at his head. "Dude!" He ducked again when a few more packets joined the first one. "Love Hearts?"

James smirked as he grabbed a box of Jaffa Cakes and sat down on one of the beds. "So you can tell the person you care about your feelings in sweet form."

Castiel tilted his head, narrowly avoiding getting hit in the side of his head with a bag of mint humbugs.

"It's all the good stuff too," Dean commented, having a look at the drinks. He helped himself to a bottle of beer, handed a bottle of whiskey to James, passed a bottle to Sam and Castiel and settled down next to James on the bed.

"Need to get sloshed," James stated, as he opened the bottle of whiskey. "Especially after the demons."

"What's sloshed?" Dean wondered, twisting open the beer cap.

It was Castiel who answered. "Drunk."

"How do you know that, Cas?"

"The internet," Castiel replied, after a slight hesitation. "It's very useful."

"It's not just for porn," James commented, pouring himself another drink. "No matter what Avenue Q says."

"I don't understand that reference," Castiel stated.

"Oh, Cas, we so need to expand your pop culture knowledge," Sam stated with a smile.

 

A few hours later, Dean leaned against James on one of the motel beds and rested his head on the red head's shoulder. On the other bed, Sam and Castiel were in a similar position with Castiel being the one leaning on Sam. "Ya know, James, it's hard to believe that you're the newest one here. We should have a party," Dean said as he drank his beer.

James frowned and took a swig from the bottle of whiskey. "For what? Not dying again?" he asked sarcastically in his deep Scottish accent.

"When you join Team Free Will, you have to die before you can be a full member," Sam stated as he wrapped an arm around Castiel's shoulder, pulling the angel closer to him.

James shrugged. "Done enough of that in Cardiff," he pointed out in a mysterious tone of voice. He raised an eyebrow at Sam's actions and let a mischievous smirk grace his face. "Is there something we should know, Sam?" he teased.

Sam blushed. "No. Just getting comfortable."

Dean snorted, all tact lost. "Yeah right." He yelped when James poked him in the side. "No prodding the merchandise, MacLeod."

"Connor or Duncan?" James retorted.

"Dude, I can't believe you know who the Highlander is. You're British."

"We get cable," James stated, "and we do have that newfangled thing known as DVDs."

"Cas is being very quiet. Has he fallen asleep?" Dean asked, craning his neck to look at the other bed.

"No. I was merely trying to comprehend your way of speaking," Castiel said, lifting his head off Sam's shoulder and turning to look at Dean and James.

"James is confusing to all," Dean said, getting another poke in the ribs. "Ow! I warned you, MacLeod."

"About what?"

"Poking me."

"Just ignore him, Cas," Sam said, seeing the look on James' face. "I think James likes to slip into the Brit slang just to be confusing."

"Me?" James asked innocently, though the mischievous twinkle in his eyes said otherwise.

"Yeah. You're a whole lot of mystery wrapped up in a mysterious taco." Sam commented, wondering if Dean's nickname of 'MacLeod' for James was a little close to the mark but shrugged it off as Castiel would be sure to say something if that was true.

"Nothing mysterious about me. I'm an open book."

"Something of you is definitely open," Dean mumbled into his beer, earning another sharp poke in the side. "Ow!"

"Word of advice, Dean," James said in a cheerful tone, "don't make comments when you're sitting within reach of the person you're talking about."

"Bastard."

"My parents were married when they had us," James retorted. He looked over to Sam and Castiel on the other bed. "Hey guys, when's the wedding?" he teased.

"Yeah, who'd be wearing the dress?" Dean added with a smile.

Sam blushed but managed to retort, "when you two agree to be bridesmaids." He looked at Castiel. "Don't you agree, Cas? Don't you think they'd both look nice in dresses?"

Castiel tilted his head. "I do not believe that they like that idea," he said, noticing the looks that James and Dean were shooting Sam. "But, yes, I believe they'd be able to pull it off very well."

 

TBC


End file.
